Phosgene → 7-(Trifluoromethyl)-1H-benzo[d][1,3]oxazine-2,4-dione

HRID 542801Notes

Reaction equation

HRID 542801 reaction equation
[C:1](Cl)(Cl)=[O:2].[NH2:5][C:6]1[CH:14]=[C:13]([C:15]([F:18])([F:17])[F:16])[CH:12]=[CH:11][C:7]=1[C:8]([OH:10])=[O:9].C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.O>[F:18][C:15]([F:16])([F:17])[C:13]1[CH:12]=[CH:11][C:7]2[C:8](=[O:10])[O:9][C:1](=[O:2])[NH:5][C:6]=2[CH:14]=1

Participants

6

Reactant 3

HCID 6371PhosgeneHCID 10340Sodium CarbonateHCID 678694-(Trifluoromethyl)anthranilic acid

Product 1

HCID 115795307-(Trifluoromethyl)-1H-benzo[d][1,3]oxazine-2,4-dione

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

A solution of phosgene (9.9 g) in toluene (100 ml) was added dropwise to a stirred solution of 2-amino-4-trifluoromethylbenzoic acid (6.9 g) and sodium carbonate (3.2 g) in water (100 ml) cooled in ice. Coolant was removed, the mixture was stirred for 2 hours, and the resulting solid was collected by filtration. The solid was dissolved in ethyl acetate and the solution was dried over anhydrous magnesium sulphate and then evaporated under reduced pressure. The resulting solid was crystallised from ethyl acetate to give the novel compound 7-trifluoromethyl-1H-3,1-benzoxazine-2,4-dione, m.p. 243°-245° (dec.)

Workup

  1. temperaturecooled in ice
  2. customCoolant was removed
  3. filtrationthe resulting solid was collected by filtration
  4. dissolutionThe solid was dissolved in ethyl acetate
  5. dry with materialthe solution was dried over anhydrous magnesium sulphate
  6. customevaporated under reduced pressure
  7. customThe resulting solid was crystallised from ethyl acetate

Sources & evidence

ORD record
ord-8dc1913296fe4807abb3dfb3f553ed9b
Source dataset
uspto-grants-1987_04
Patent number
US04659718

Reaction notes

Loading…